Tryptamine analogs

Shulgin, A. T., and Carter, M. F. (1981) N,N-Diisopropyltryptamine (DIPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO DIPT). Two orally active tryptamine analogs with CNS activity. Commun. Psychopharmacol., 4 363-369. 

Abate C, Kolanos R, Dukat M, Setola V, Roth B, Glennon RA. Interaction of chiral tryptamine analogs at / 5-HT6 serotonin receptors. Bioorg Med Chem Lett 2005 15 3510-3513. 

Cyanomethylindole 12d also proved to be a versatile intermediate toward the synthesis of sumatriptan (Scheme 4).7,8 Hydrogenation of the cyano group of 12d m the presence of dimethylamine provided sumitriptan (1) directly, which was isolated as the hemisuccinate salt. Alternatively, the cyano group of 12d was hydrolyzed to the carboxylic acid (18) and then transformed into the dimethyl amide 19. Finally, the amide was reduced with LiAlHt to afford sumatriptan (1). Although this is a longer synthesis of 1, the intermediate 18 allows for the preparation of various tryptamine analogs. 

Benziminazole analog of 5-OH-tryptamine JCS 1671(1957) 5-BR-benzoihiophene analog of DMT JMC 10,270(1967) Tryptamine analogs using pyrrolidine and piperidine JMC 10,1015... 

Dimerization is also prevented by the presence of a formal positive charge on a j8-substituent, thus tryptamine cannot be dimerized. The formation of the trimer can be rationalized by analogy with the reactions of gramine and its derivatives. Thus, Thesing and Mayer found that methylphenylskatylamine (49) reacts with... 

This method, although described for indoles, probably also worlds with 5-OH-tryptamine (serotonin), and 5-OH-DMT (bufotenin) with compounds of the latter type, orally active psilocybin analogs will be obtained in one step. Dissolve 5 g 5-OH-indole (or analog) in 25 ml ethanol. Add 5.5 g 33% aqueous dimethylamine (or other amine, e.g., piperidine) and add slowly dropwise with stirring 3.5 g 38% aqueous formaldehyde. Two minutes after the end of the addition shake with water and CHCI3 dry and evaporate in vacuum the CHClj phase to get 5 g oily 4-dimethyl-aminomethyl-5-OH-indole (1) (can chromatograph on 100 g alumina and elute with ethyl acetate). It has been claimed that this method does not work. 

CA 79,146321(1973) gives a one step synthesis of tryptamine from phenylhydrazine and 4-chlorobutyraldehyde by refluxing in aqueous ethanol for 6 hours (70% yield). CA 80,3381(1974) gives the preparation of DMT analogs. 

Dissolve 4 g glyoxylic acid monohydrate in 220 ml water and add with stirring to a solution of 10 g 4,5, or 6 methoxy-tryptamine-HCl in 80 ml water. Adjust pH to 4 with 10% KOH and stir five hours at room temperature. Filter and wash with water to get about 4.5 g precipitate. Melt to decarboxylate or to 4 g precipitate add 30 ml concentrated HCI and 100 ml water and heat at 65° one hour. Add water to dissolve the solid and add excess 10% KOH. Filter to get the title compound or analog. 

Harmaline and analogs BSC 2058(1973). Beta-carbolines from sugars and tryptamines in 1 step BER 106,2943(1973). 

Dialkyltryptamines from Tryptamines. Bull. Chem. Soc. Jap. Vol. 11, 221 (1936). 1.5 g of tryptamine is mixed by gentle stirring with 30 ml of ethanol (dry). Add 5 g of methyl iodide and 4.5 g of dry sodium carbonate and heat five hours (just below reflux temp) on a water bath. Filter hot, heat precipitate with ethanol and filter hot again. Evaporate the ethanol off in vacuo to get about 2 A g of 1-methyl-DMT or analog. 

Some neuroleptic agents, like cycloindole (497), which has a modified tryptamine structure, and flucindole (498), a difluoro analog of cycloindole, have found use in therapy because of their anti-depressant and anti-psychotic activity (463,464) (Scheme 4.11). 3-Chlorocarbazole (385) (see Scheme 2.102), isolated from female bovine urine, has Diazepam-like activity (354). 

Mit Tryptamin in Benzol/Tetrahydrofuran (1 1) erhalt man analog 3-[2-(4-Acetoxyme-thyl-2-cyclohexen-l-ylamino)-ethyl]-indol. 

EXTENSIONS AND COMMENTARY The relationship between a-MT (alpha-methyl tryptamine) and this compound, a,N-DMT (alpha,N-dimethyltryptamine) is exactly analogous to that seen with the phenethylamine counterparts, between amphetamine (alpha-... 

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